30418-59-8

Basic information

• Product Name: 3-Aminobenzeneboronic acid
• Synonyms: 3-Aminophenylboronic Acid Monohydrate (contains varying amounts of Anhydride);3-Aminobenzeneboronic acid, 96.5+%;3-Aminophenylboranic acid;3-Aminophenyldihydroxyborane;(3-azanylphenyl)boronic acid;3-Boronoaniline;Boronic acid,B-(3-aMinophenyl)-;3-Aminobenzeneboronic acid 3-Aminophenylboronic acid
• CAS NO: 30418-59-8
• Molecular Formula: C₆H₈BNO₂
• Molecular Weight: 136.94
• EINECS: 250-189-0
• Product Categories: B (Classes of Boron Compounds);Boronate Ester;Potassium Trifluoroborate;Amines;blocks;BoronicAcids;Boronic acids;Boronic Acid
• Mol File: 30418-59-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 98°C
• Boiling Point: 376 °C at 760 mmHg
• Flash Point: 181.2 °C
• Appearance: light yellow crystalline solid
• Density: 1.23 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: pK1: 4.46;pK2: 8.81 (25°C)
• Water Solubility: Soluble in water (partly miscible).
• CAS DataBase Reference: 3-Aminobenzeneboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminobenzeneboronic acid(30418-59-8)
• EPA Substance Registry System: 3-Aminobenzeneboronic acid(30418-59-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 30418-59-8(Hazardous Substances Data)

Usage

Chemical Properties

hexagonal plates

Uses

Different sources of media describe the Uses of 30418-59-8 differently. You can refer to the following data:
1. suzuki reaction
2. 3-Aminobenzeneboronic acid is a boronic acid with potential use for biochemical research,it ie also used for suzuki reaction.
3. 3-Aminobenzeneboronic acid is used as an organic chemical synthesis intermediate. It is a boronic acid with potential use for biochemical research.

InChI:InChI=1/C6H8BNO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H,8H2

Synthetic route

m-nitrobenzene boronic acid (13331-27-6) → 3-Aminophenylboronic acid (30418-59-8)

Conditions	Yield
Stage #1: m-nitrobenzene boronic acid With hydrogenchloride; 1,1,1,3',3',3'-hexafluoro-propanol; iron In water at 20℃; for 0.5h; Stage #2: With sodium hydrogencarbonate In water chemoselective reaction;	83%
With methanol; platinum Hydrogenation;
With barium dihydroxide; iron(II) hydroxide; water
With hydrogen; platinum(IV) oxide In methanol; water under 3102.97 Torr; for 0.75h;
With hydrogen In methanol at 20℃; under 775.743 Torr; for 20h;

potassium 3-aminophenyltrifluoroborate (1160186-73-1) + water (7732-18-5) → 3-Aminophenylboronic acid (30418-59-8)

Conditions	Yield
With montmorillonite K10 at 25℃; for 1.5h;	78%

3-Bromonitrobenzene (585-79-5) + 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) → 3-Aminophenylboronic acid (30418-59-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium acetate In dimethyl sulfoxide at 90℃; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;	71%

3-aminophenylboronic acid hydrogen sulphate → 3-Aminophenylboronic acid (30418-59-8)

Conditions	Yield
With sodium hydroxide In water pH=7.2;	66%

2-(3-aminophenyl)-4-{[tris-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silanyl]methyl}[1,3,2]dioxaborolane → 3-Aminophenylboronic acid (30418-59-8)

Conditions	Yield
With acetic acid In tetrahydrofuran; water at 20℃;

phenylboronic acid (98-80-6) → 3-Aminophenylboronic acid (30418-59-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: urea; nitric acid 2: iron (II)-hydroxide; barium hydroxide; water View Scheme

3-aminophenylboronic acid hydrochloric salt → 3-Aminophenylboronic acid (30418-59-8)

Conditions	Yield
With NaF; Nafion solution In hydrogenchloride Electrochem. Process; on glassy carbon electrode according to Nicolas, M., et al., J. Eur. J. Org. Chem., 2000, 9, 1703-1710; NH2C6H4B(OH)2*HCl, NaF (40 mM) dissolvedin 0.2 M HCl; Nafion soln. added; mixt. vigorously stirred; potential w as scanned between 0.0 and +1.1 V...;
With NaF In hydrogenchloride Electrochem. Process; on glassy carbon electrode according to Nicolas, M., et al., J. Eur. J. Org. Chem., 2000, 9, 1703-1710; NH2C6H4B(OH)2*HCl, NaF (200 mM) dissolved in 0.5 M HCl; mixt. vigorously stirred; potential was scanned between 0.0 and +1.1 V in the unstirred soln.;

3-aminophenylboronic acid hemisulfate → 3-Aminophenylboronic acid (30418-59-8)

Conditions	Yield
With sodium hydroxide In water at 0 - 5℃; pH=7.2;	21.7 g

3-bromoaniline (591-19-5) → 3-Aminophenylboronic acid (30418-59-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / 150 h / Reflux; Large scale 2: n-butyllithium / tetrahydrofuran; hexane / -80 °C / Inert atmosphere 3: sodium hydroxide / water / 0 - 5 °C / pH 7.2 View Scheme
Multi-step reaction with 3 steps 1: toluene / Reflux; Large scale 2: n-butyllithium / tetrahydrofuran; hexane / -80 °C / Inert atmosphere 3: sodium hydroxide / water / 0 - 5 °C / pH 7.2 View Scheme

3-bromo-N-(diphenylmethylene)-benzenamine (1020180-02-2) → 3-Aminophenylboronic acid (30418-59-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / -80 °C / Inert atmosphere 2: sodium hydroxide / water / 0 - 5 °C / pH 7.2 View Scheme

3-Aminophenylboronic acid (30418-59-8) + 4-nitrophenyl-α-D-mannopyranoside (10357-27-4) → 4'-nitrophenyl α-D-mannopyranoside-2,3,4,6-di-O-(3"-aminophenylboronate)

Conditions	Yield
In 1,4-dioxane	100%

Pd(0) + Na2 CO3 + (R)-2-((5-bromopyridin-3-yloxy)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester (228867-10-5) + 3-Aminophenylboronic acid (30418-59-8) → 5-(3-aminophenyl)-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine (191162-60-4)

Conditions	Yield
In toluene	100%

3-(6-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine (863783-61-3) + 3-Aminophenylboronic acid (30418-59-8) → 3-[4-(5,6-Dimethyl-[2,2']bipyridin-3-yloxy)-quinolin-6-yl]-phenylamine

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 70℃;	100%

3-(7-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine (863783-73-7) + 3-Aminophenylboronic acid (30418-59-8) → 3-[4-(5,6-Dimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-yl]-phenylamine

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 70℃; for 5h;	100%

6-bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (927389-32-0) + 3-Aminophenylboronic acid (30418-59-8) → 6-(3-aminophenyl)-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (927391-06-8)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 20 - 95℃; for 12h;	100%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 100℃; for 17h; Inert atmosphere;

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol (7591-01-7) + 3-Aminophenylboronic acid (30418-59-8) → 4'-nitrophenyl α-D-mannopyranoside-2,3,4,6-di-O-(3"-aminophenylboronate)

Conditions	Yield
In 1,4-dioxane dehydration (azeotropic distillation) of the 1:2 mixture of starting materials in dioxane;	100%

3-Aminophenylboronic acid (30418-59-8) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)aniline (220080-93-3)

Conditions	Yield
In dichloromethane for 24h;	100%
In chloroform for 12h;	99%
In chloroform at 20℃; for 6h;	80.9%
In toluene at 20℃; for 12h;
In chloroform at 20℃;

Upstream product

• 585-79-5 m-nitrobromobenzene 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 1160186-73-1 potassium 3-aminophenyltrifluoroborate 
• 7732-18-5 water 
• 1020180-02-2 3-bromo-N-(diphenylmethylene)-benzenamine 
• 591-19-5 m-Bromoaniline 
• 85006-23-1 3-aminophenylboronic acid hydrochloric salt 
• 98-80-6 phenylboronic acid 
• 13331-27-6 m-nitrobenzene boronic acid 

Downstream Products

• 90084-66-5 m-ureidophenylboronic acid 
• 109445-19-4 3-(nicotinamidophenyl)boronic acid 
• 87199-18-6 3-hydroxyphenylboronic acid 
• 100607-14-5 (3-((ethoxycarbonyl)amino)phenyl)boronic acid 
• 184041-22-3 N-(3-methyl-5-isoxazolyl)-5-(3-aminophenyl)thiophene-2-sulfonamide 
• 133887-74-8 3-Isothiocyanatophenylboronic acid 
• 15889-32-4 3-(2-pyridyl)aniline 
• 57976-57-5 3-(pyridin-3-yl)aniline 
• 40034-44-4 3-(pyridin-4-yl)benzenamine 
• 380430-68-2 3-(tert-butoxycarbonylamino)phenylboronic acid 
• 158014-73-4 4'-(3'''-aminophenyl)-2,2':6,2''-terpyridine 
• 441348-00-1 methyl O-(3'-amino-1,1'-biphenyl-4-yl)-N-triphenylmethyl-L-serinate 

Relevant articles and documents

Method for synthesizing 3-aminobenzeneboronic acid

The invention discloses a method for synthesizing 3-aminobenzeneboronic acid, and belongs to the field of organic synthesis. The method comprises the following steps: performing coupling reaction on 3-nitrobromobenzene and catechol diboron under action of a palladium catalyst; adding water for quenching; adding an acid for salifying a product and entering a water layer; adding alkali into the separated water layer to adjust to near neutral; and extracting and desolventizing to obtain the 3-aminobenzeneboronic acid. The method is simple in operation, high in purity of the obtained product and suitable for industrialized scale-up production.

An efficient method for the hydrolysis of potassium organotrifluoroborates promoted by montmorillonite K10

An efficient and non-expensive method for conversion of diverse potassium organotrifluoroborates to their corresponding boronic acids promoted by montmorillonite K10 using water as the reaction solvent is described. Further interconversion of potassium organotrifluoroborates to their corresponding boronic esters, via boronic acid intermediates was also successfully accomplished. The products were obtained in good yields, being the rate of hydrolysis influenced by the type of substituent present in the boronic acid.

PROCESS FOR THE PREPARATION OF AMINOARYL- AND AMINOHETEROARYL BORONIC ACIDS AND ESTERS

The present invention relates to a process for the preparation of aminoaryl- and aminoheteroaryl boronic acids and esters thereof of formula (I) in high yield. The claimed process uses diarylketal formula (V) to generate an arylbromide of formula (III) in which the amino-group is protected as bisarylmethylidenimino-group, which is then transformed into a formula (I) compound.